Vat dyestuffs



Patented Mar. 4, 193i) UNITED STATES PATENT OFFICE HEINRICH NEIBISHEIIEB AND WILHELM SGfiNEIDER, OF LUDWIGSHAI'EN-ON-THE" BHINE, GERMANY, ABSIGNOBS T GENERAL ANILINE WORKS, INC., 01 NEW YORK,

rr. "2., a conroanrrou' or nmwm VAT DYESTUFIS )l'o Drawing. Application filed November 8, 1927, Serial No. 582,188, and in Germany November 15, 1828.

Red vat dyestuffs are already known, .derived from 1-acylamino-4-hydroxyanthraquinones by the substitution of the hydroxyl group with the radicles of monovalent 5 alcohols. As a rule these products dye cotton onl from cold vats.

We ave now found that vat dyestuffs constitution Nn-oo-oan Na-oo-oan 1o I 00 00 o0 and p oo co l 5 onr-om-o1 -om-om-on 65 which will dye from warm vats also, and (give 1 much more yellowish shades are obtaine by introducing radicles of polyvalent alcohols into the hydroxyl group or groups of 1- acylamino 4-hydroxy-anthraquinones. These vat dyestufls may be prepared for example,

by .treating the l-acylaminoi-hydroxyanthraquinones with suitable esters, such as the halogen hydrid esters or aryl-sulfonic esters of polyvalent alcohols, in the-presence of-substances capable of combining with acids. Dependin on the conditions of working the acid {a iclesnff the esfirs ustled 1153 b; conilete or o partia rep ace -acy 80 smino lrhydrgxyanthrazuinone radibles. In the case of a partial replacement, hydroxyl groups may in some instances be substituted, y a secondary reaction, for the unexchanged acid radicles.

The resulting vat dyestufis give bright oranged ejngs, with excellent roperties as regards astne'ss, on vegetable bres, from both cold and warm vats.

The following examples will further illustrate how the said invention maybe carried into practical effect but the invention isnot limited thereto. The parts are by weight.

Efavample 1 10 parts of l-benzo lamino-4-hydroxyanthraquinone are boil with-10 parts of ptoluenesulfonic acid chlorethyl ester and 10 parts of calcined soda in 100 parts of trichlorbenzene, until benzoyl'ammo-hydroxyanthraquinone can no longer be detected.

' ponent indicate that it probab y consists of a The resulting dyestufi can be separated into two components by crystallization, for ex ample, from nitrobenzene. The analysis and properties of the more readil soluble commixture of two substances of the following The product gives yellow dyeings with an orange tinge on cotton from a vat of the same color. Boiling with soap develops the color to a brilliant red-orange.

- he component whi h is less readily soluble in nitrobenzene, and has, from analysis, the probable constitution is very similar, in tinctorial properties, to the more soluble product.

'- Ewample 2 according to Example 1.

Example 8 i If the 1-benzoylamino4-hydroxyanthraquinone used in Example 2 be replaced 1- 'm-methoxybenzoylarnino' 4 -hydroxyant 1-.-

quinone, a vat dyestufi is obtained which givespowerful yellow-orange dyeings on vegetable fibres, the color of wnich is not modified by boiling soap.

Example 4 If the di-p toluenesulfonic acid ester ofethyleneglycol used in Example 2 be replaced by glycerol-tri-p-toluenesulfonic ester, a dyestufi' of very similar shade to that obtained according to Example 2 is produced.

What'we claim is:

1. The process for the production of orange-colored vat dyestufi's of the anthraquinone series, which consists in acting on a 1-acylaminol-hydroxy-anthraquinone with an agent capable of supplying a radicle of a polyvalent alcohol.

2. The process for the production of orange-colored vat dyestufis of the anthraquinone series, which consists in introducing radicles of polyvalent alcohols into the hydroxyl groups of l-acylamino-4-hydroxy -anthraquinones.

3. The process for the production of orange-colored vat dyestuffs of the anthraquinone series, which consists in treating l-acylamino-4-hydroxyanthraquinones with esters of pol valent alcohols containing an easily iuterc angeable acid residue in the presence of a substance capable of combining with acids. I

4. The process for the production of an orange-colored vat dyestuff of the anthraquinone series, which consists in treating 1 benzoylamino 4 hydroxyanthraquinone with the di-p-toluene-sulfonic acid ester of ethylene glycol in the presence of a substance capable of combining with acids.

5. As new articles of manufacture orange vat dyestuffs of the anthraquinone series being probably l-acylaminoi-hydroxyanthraquinones in which the h droxyl groups are substituted by radicles o polyvalent alcohols, substantially as described.

6. As new article of manufacture the orange vat dyestufi' probably having the constitution:

- NH-C 0.00111 NH.OO.C;H|

co co CHi-CH,- 

